Chicago Up High: Views From the Top

Chicago is generally considered to be the birthplace of the skyscraper. The city experienced a period of exceptional growth after a devastating fire in 1871 razed an area of more than three square miles to the ground, and before too long the city limits were straining against a tide of new developments. The only solution was to build upwards.

With no more land to play with, new steel construction techniques were developed to ensure a new generation of tall buildings could withstand any stresses or strains and forces of nature. And so the skyscraper era was born, and the race for the clouds had begun.

Now the Windy City has a skyline to rival New York, and there are many who would say it surpasses it. To judge for yourself, there are plenty of options for getting up close to Chicago’s architecture; one of the best being the Chicago Architecture Foundation Boat Tours which take an in-depth look at more than 50 significant buildings on a 90-minute cruise up the Chicago River. But to really appreciate the compressed nature of the city’s tightly-packed vertical core, you’ll need to gaze down on it from above. Two of Chicago’s biggest attractions compete with each other to offer the best skyline views…

Willis Tower – Skydeck Chicago

Formerly the tallest building in the western hemisphere – before the completion of NYC’s One World Trade Center – Willis Tower, previously known as the Sears Tower, is a corporate office building and Chicago’s most recognisable landmark. It is home to more than 100 companies.

Willis Tower and Chicago Skyline from the 16th Street Bridge John Picken

From the 1,353 feet high observation Skydeck on the 103rd floor, you can see four different states – Illinois, Indiana, Michigan and Wisconsin – with visibility of up to 40-50 miles on a clear day. Better still is the early evening view, when the lights of the city start to twinkle. Head up about an hour before sunset to get the full experience of daylight, twilight and nighttime views – visit sunrisesunset.com to perfectly time your trip.

You won’t get a higher viewpoint anywhere else in the city, but if you’re seeking extra thrills then dare to step out onto The Ledge and look down. These four glass boxes extend 4.3 feet out from the Skydeck over Wacker Drive and the Chicago River. Each box is made of three layers of half-inch thick glass laminated into one seamless unit, and provide unobtrusive if vertigo-inducing views.

The Skydeck is open every day from 9am – 10pm (summer) and 10am – 8pm (winter). Tickets are $19.50 for adults and $12.50 for children, or visit with a Chicago CityPass.

360° Chicago at the John Hancock Center

The 360° Chicago observatory deck is not quite as high as the one at Willis Tower, but it arguably has a better location – north of The Loop and closer to the lakeside, offering jaw-dropping views over Lake Michigan and the Magnificent Mile.

You can step right out into the fresh air on the Skywalk; the highest public, open-air viewing deck in the Midwest, and discover firsthand why they call it the Windy City. Inside, the not-for-the-fainthearted Tilt feature holds up to 8 people, and offers bird’s eye, downward views over the Magnificent Mile and the famous skyline, as it extends outwards from 1,000 feet up.

The 360° Chicago observatory has some of the fastest lifts in North America, whisking you from ground level to 1,000 feet in 40 seconds. Take them up one more level to the Signature Room at the 95th and enjoy a fine dining experience in a glamorous art deco setting with floor-to-ceiling views of the Chicago skyline.

360° Chicago is open daily from 9am to 11pm (last admission 10.30pm). Tickets are $19 for adults, $13 for children, or you can buy a Sun & Stars pass for $21/$15 which allows 2 visits in 48 hours to make the most of the views at different times of day. Admission is also available as part of the Chicago CityPass.

Virgin Atlantic operates a seasonal summer service with daily direct flights to Chicago from London Heathrow.